Crystal structure of 2-(3-fluoro-phen-yl)-5-iodo-3-methyl-sulfinyl-1-benzo-furan.

In the title compound, C15H10FIO2S, the dihedral angle between the planes of the benzo-furan ring system [r.m.s. deviation = 0.015 (2) Å] and the 3-fluoro-phenyl ring is 29.63 (7)°. In the crystal, mol-ecules are linked into inversion dimers along the b-axis direction by two different pairs of C-H⋯O hydrogen bonds and I⋯O [3.228 (1) Å] contacts.

Related literature

For a related structure and background to benzo­furan derivatives, see: Choi & Lee (2014 ▶). For further synthetic details, see: Choi et al. (1999 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C15H10FIO2S

M = 400.19

Triclinic,

a = 8.1348 (3) Å

b = 8.6378 (3) Å

c = 10.8350 (4) Å

α = 86.063 (1)°

β = 82.088 (1)°

γ = 66.408 (1)°

V = 690.99 (4) Å3

Z = 2

Mo Kα radiation

μ = 2.48 mm−1

T = 173 K

0.45 × 0.28 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.496, T max = 0.746

12585 measured reflections

3450 independent reflections

3226 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.054

S = 1.05

3450 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814022569/qm2109sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814022569/qm2109Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814022569/qm2109Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814022569/qm2109fig1.tif

The mol­ecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

Click here for additional data file.

x y z x y z x y z . DOI: 10.1107/S1600536814022569/qm2109fig2.tif

A view of the C—H⋯O and I⋯O inter­actions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) −x, −y + 2, −z + 1; (ii) −x + 2, −y + 1, −z; (iii) −x + 1, −y + 2, −z + 2.]

CCDC reference: 1029138

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H10FIO2S	Z = 2
Mr = 400.19	F(000) = 388
Triclinic, P1	Dx = 1.923 Mg m−3
Hall symbol: -P 1	Melting point = 454–453 K
a = 8.1348 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6378 (3) Å	Cell parameters from 8421 reflections
c = 10.8350 (4) Å	θ = 2.6–28.4°
α = 86.063 (1)°	µ = 2.48 mm−1
β = 82.088 (1)°	T = 173 K
γ = 66.408 (1)°	Block, colourless
V = 690.99 (4) Å3	0.45 × 0.28 × 0.11 mm

Bruker SMART APEXII CCD diffractometer	3450 independent reflections
Radiation source: rotating anode	3226 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 1.9°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
Tmin = 0.496, Tmax = 0.746	l = −14→14
12585 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.021	Hydrogen site location: difference Fourier map
wR(F2) = 0.054	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0277P)2 + 0.2506P] where P = (Fo2 + 2Fc2)/3
3450 reflections	(Δ/σ)max = 0.002
182 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −0.59 e Å−3

Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 8.59 (s, 1H), 7.70 (dd, J =8.56 and 1.72 Hz, 1H), 7.46-7.62 (m, 3H), 7.36 (d, J =8.88 Hz, 1H), 6.16-7.22 (m, 1H), 3.11 (s, 3H).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
I1	0.171392 (16)	1.149394 (16)	1.025925 (12)	0.03179 (6)
S1	0.78329 (6)	0.70139 (6)	0.61226 (5)	0.02565 (10)
F1	0.44813 (19)	0.69674 (18)	0.05731 (12)	0.0428 (3)
O1	0.29753 (17)	0.86217 (16)	0.49979 (13)	0.0257 (3)
O2	0.81435 (19)	0.83024 (18)	0.67958 (15)	0.0322 (3)
C1	0.5521 (2)	0.7849 (2)	0.59123 (18)	0.0236 (4)
C2	0.4042 (2)	0.8963 (2)	0.67518 (18)	0.0229 (3)
C3	0.3844 (2)	0.9583 (2)	0.79446 (18)	0.0245 (4)
H3	0.4851	0.9312	0.8393	0.029*
C4	0.2108 (2)	1.0612 (2)	0.84450 (18)	0.0252 (4)
C5	0.0602 (3)	1.1041 (2)	0.77957 (19)	0.0279 (4)
H5	−0.0560	1.1753	0.8173	0.033*
C6	0.0793 (3)	1.0437 (2)	0.6614 (2)	0.0280 (4)
H6	−0.0209	1.0718	0.6158	0.034*
C7	0.2528 (2)	0.9398 (2)	0.61297 (18)	0.0240 (4)
C8	0.4815 (2)	0.7686 (2)	0.48808 (18)	0.0239 (4)
C9	0.5539 (2)	0.6727 (2)	0.37323 (18)	0.0246 (4)
C10	0.7027 (3)	0.5184 (2)	0.36961 (19)	0.0284 (4)
H10	0.7611	0.4757	0.4422	0.034*
C11	0.7657 (3)	0.4272 (3)	0.2604 (2)	0.0298 (4)
H11	0.8680	0.3228	0.2583	0.036*
C12	0.6806 (3)	0.4872 (3)	0.1544 (2)	0.0310 (4)
H12	0.7223	0.4250	0.0794	0.037*
C14	0.4675 (3)	0.7348 (2)	0.26611 (18)	0.0259 (4)
H14	0.3661	0.8396	0.2666	0.031*
C13	0.5339 (3)	0.6395 (3)	0.16068 (19)	0.0296 (4)
C15	0.7795 (3)	0.5423 (3)	0.7268 (2)	0.0399 (5)
H15A	0.8990	0.4863	0.7554	0.060*
H15B	0.7483	0.4587	0.6898	0.060*
H15C	0.6893	0.5949	0.7976	0.060*

	U11	U22	U33	U12	U13	U23
I1	0.02741 (8)	0.03722 (9)	0.02882 (8)	−0.01142 (6)	0.00213 (5)	−0.00751 (6)
S1	0.01711 (19)	0.0255 (2)	0.0331 (2)	−0.00688 (17)	−0.00367 (17)	−0.00041 (18)
F1	0.0462 (8)	0.0463 (8)	0.0316 (7)	−0.0101 (6)	−0.0147 (6)	−0.0038 (6)
O1	0.0192 (6)	0.0277 (7)	0.0269 (7)	−0.0050 (5)	−0.0048 (5)	−0.0025 (5)
O2	0.0279 (7)	0.0310 (7)	0.0421 (8)	−0.0142 (6)	−0.0108 (6)	0.0011 (6)
C1	0.0189 (8)	0.0222 (8)	0.0287 (9)	−0.0072 (7)	−0.0034 (7)	0.0005 (7)
C2	0.0187 (8)	0.0212 (8)	0.0283 (9)	−0.0078 (7)	−0.0032 (7)	0.0020 (7)
C3	0.0205 (8)	0.0259 (9)	0.0272 (9)	−0.0089 (7)	−0.0043 (7)	0.0010 (7)
C4	0.0232 (8)	0.0245 (9)	0.0279 (9)	−0.0100 (7)	−0.0014 (7)	−0.0001 (7)
C5	0.0204 (8)	0.0254 (9)	0.0341 (10)	−0.0059 (7)	−0.0007 (7)	−0.0007 (8)
C6	0.0184 (8)	0.0292 (9)	0.0340 (10)	−0.0059 (7)	−0.0063 (7)	0.0000 (8)
C7	0.0218 (8)	0.0235 (8)	0.0254 (9)	−0.0074 (7)	−0.0045 (7)	0.0004 (7)
C8	0.0181 (8)	0.0215 (8)	0.0295 (9)	−0.0060 (7)	−0.0019 (7)	0.0019 (7)
C9	0.0228 (8)	0.0258 (9)	0.0280 (9)	−0.0127 (7)	−0.0025 (7)	−0.0013 (7)
C10	0.0248 (9)	0.0283 (9)	0.0305 (10)	−0.0085 (7)	−0.0042 (7)	−0.0010 (8)
C11	0.0225 (9)	0.0270 (9)	0.0363 (11)	−0.0066 (7)	−0.0002 (8)	−0.0030 (8)
C12	0.0284 (9)	0.0331 (10)	0.0318 (10)	−0.0128 (8)	0.0008 (8)	−0.0076 (8)
C14	0.0224 (8)	0.0254 (9)	0.0307 (9)	−0.0101 (7)	−0.0043 (7)	0.0009 (7)
C13	0.0291 (9)	0.0342 (10)	0.0283 (10)	−0.0148 (8)	−0.0061 (8)	0.0000 (8)
C15	0.0357 (11)	0.0310 (11)	0.0560 (14)	−0.0147 (9)	−0.0186 (10)	0.0156 (10)

I1—C4	2.0937 (19)	C6—C7	1.385 (3)
I1—O2i	3.2282 (16)	C6—H6	0.9500
S1—O2	1.4906 (15)	C8—C9	1.460 (3)
S1—C1	1.7660 (18)	C9—C10	1.396 (3)
S1—C15	1.794 (2)	C9—C14	1.402 (3)
F1—C13	1.360 (2)	C10—C11	1.386 (3)
O1—C7	1.371 (2)	C10—H10	0.9500
O1—C8	1.380 (2)	C11—C12	1.385 (3)
C1—C8	1.364 (3)	C11—H11	0.9500
C1—C2	1.447 (2)	C12—C13	1.376 (3)
C2—C7	1.392 (3)	C12—H12	0.9500
C2—C3	1.397 (3)	C14—C13	1.370 (3)
C3—C4	1.389 (2)	C14—H14	0.9500
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.404 (3)	C15—H15B	0.9800
C5—C6	1.382 (3)	C15—H15C	0.9800
C5—H5	0.9500
C4—I1—O2i	162.99 (6)	C1—C8—C9	135.08 (17)
O2—S1—C1	107.27 (8)	O1—C8—C9	114.36 (16)
O2—S1—C15	105.59 (11)	C10—C9—C14	119.72 (18)
C1—S1—C15	97.77 (10)	C10—C9—C8	121.22 (18)
C7—O1—C8	106.51 (14)	C14—C9—C8	119.02 (17)
C8—C1—C2	107.22 (16)	C11—C10—C9	120.19 (19)
C8—C1—S1	126.32 (14)	C11—C10—H10	119.9
C2—C1—S1	126.23 (14)	C9—C10—H10	119.9
C7—C2—C3	119.44 (16)	C12—C11—C10	120.41 (19)
C7—C2—C1	104.72 (16)	C12—C11—H11	119.8
C3—C2—C1	135.82 (17)	C10—C11—H11	119.8
C4—C3—C2	116.96 (17)	C13—C12—C11	118.20 (18)
C4—C3—H3	121.5	C13—C12—H12	120.9
C2—C3—H3	121.5	C11—C12—H12	120.9
C3—C4—C5	122.53 (18)	C13—C14—C9	117.96 (18)
C3—C4—I1	118.63 (14)	C13—C14—H14	121.0
C5—C4—I1	118.81 (13)	C9—C14—H14	121.0
C6—C5—C4	120.71 (17)	F1—C13—C14	118.31 (18)
C6—C5—H5	119.6	F1—C13—C12	118.15 (18)
C4—C5—H5	119.6	C14—C13—C12	123.5 (2)
C5—C6—C7	116.21 (18)	S1—C15—H15A	109.5
C5—C6—H6	121.9	S1—C15—H15B	109.5
C7—C6—H6	121.9	H15A—C15—H15B	109.5
O1—C7—C6	124.79 (17)	S1—C15—H15C	109.5
O1—C7—C2	111.03 (15)	H15A—C15—H15C	109.5
C6—C7—C2	124.15 (18)	H15B—C15—H15C	109.5
C1—C8—O1	110.51 (16)
O2—S1—C1—C8	141.12 (17)	C3—C2—C7—C6	0.5 (3)
C15—S1—C1—C8	−109.83 (19)	C1—C2—C7—C6	178.84 (18)
O2—S1—C1—C2	−32.64 (19)	C2—C1—C8—O1	0.0 (2)
C15—S1—C1—C2	76.41 (18)	S1—C1—C8—O1	−174.78 (13)
C8—C1—C2—C7	−0.4 (2)	C2—C1—C8—C9	−177.5 (2)
S1—C1—C2—C7	174.33 (15)	S1—C1—C8—C9	7.7 (3)
C8—C1—C2—C3	177.6 (2)	C7—O1—C8—C1	0.5 (2)
S1—C1—C2—C3	−7.7 (3)	C7—O1—C8—C9	178.56 (16)
C7—C2—C3—C4	0.2 (3)	C1—C8—C9—C10	29.0 (3)
C1—C2—C3—C4	−177.6 (2)	O1—C8—C9—C10	−148.40 (17)
C2—C3—C4—C5	−0.6 (3)	C1—C8—C9—C14	−153.2 (2)
C2—C3—C4—I1	177.44 (13)	O1—C8—C9—C14	29.3 (2)
O2i—I1—C4—C3	−46.0 (3)	C14—C9—C10—C11	0.4 (3)
O2i—I1—C4—C5	132.10 (18)	C8—C9—C10—C11	178.10 (18)
C3—C4—C5—C6	0.3 (3)	C9—C10—C11—C12	−0.7 (3)
I1—C4—C5—C6	−177.70 (15)	C10—C11—C12—C13	0.5 (3)
C4—C5—C6—C7	0.3 (3)	C10—C9—C14—C13	0.1 (3)
C8—O1—C7—C6	−178.87 (18)	C8—C9—C14—C13	−177.66 (17)
C8—O1—C7—C2	−0.8 (2)	C9—C14—C13—F1	178.38 (17)
C5—C6—C7—O1	177.14 (18)	C9—C14—C13—C12	−0.3 (3)
C5—C6—C7—C2	−0.7 (3)	C11—C12—C13—F1	−178.69 (18)
C3—C2—C7—O1	−177.65 (16)	C11—C12—C13—C14	0.0 (3)
C1—C2—C7—O1	0.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ii	0.95	2.57	3.520 (2)	177
C11—H11···O2iii	0.95	2.55	3.372 (2)	145

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C6H6O1i	0.95	2.57	3.520(2)	177
C11H11O2ii	0.95	2.55	3.372(2)	145

Symmetry codes: (i) ; (ii) .